Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester
• CAS No.: 117169-28-5
• Molecular Formula: C₃₉H₆₃F₃O₁₀SSi
• Molecular Weight: 809.07
• Mol file: 117169-28-5.mol

Synonyms:Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester

There total 12 articles about Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (4S,5S)-6-Benzyloxy-1-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-4-(2-methoxy-ethoxymethoxy)-5-methyl-hexan-3-one (117169-27-4) → Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester (117169-28-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol (74243-88-2) → Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester (117169-28-5)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH

2: HCl, EtOH

3: Et₃N, CH₂Cl₂

4: i-Pr₂NEt

5: AcOH, H₂O / 40 °C

6: PCC

7: n-BuLi / tetrahydrofuran / -78 °C

8: 1.) CrO_3.2py, 2.)Al(Hg) / 1.) aq. THF, 2.)aq. THF, 65 deg C

9: 70 percent / LiN(TMS)2 / tetrahydrofuran / -78 °C

With hydrogenchloride; aluminum amalgam; n-butyllithium; ethanol; dichloromethane; water; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

(2S,3S)-erythro-3-methylbutane-1,2,4-triol (74213-64-2) → Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester (117169-28-5)

Guidance literature:

Multi-step reaction with 10 steps

1: H+

2: NaH

3: HCl, EtOH

4: Et₃N, CH₂Cl₂

5: i-Pr₂NEt

6: AcOH, H₂O / 40 °C

7: PCC

8: n-BuLi / tetrahydrofuran / -78 °C

9: 1.) CrO_3.2py, 2.)Al(Hg) / 1.) aq. THF, 2.)aq. THF, 65 deg C

10: 70 percent / LiN(TMS)2 / tetrahydrofuran / -78 °C

With hydrogenchloride; aluminum amalgam; n-butyllithium; ethanol; dichloromethane; water; hydrogen cation; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86686-1

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(4S,5S)-6-Benzyloxy-1-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-4-(2-methoxy-ethoxymethoxy)-5-methyl-hexan-3-one

(2S,3S)-erythro-3-methylbutane-1,2,4-triol

(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol

Downstream raw materials:

[(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane

[(2R,4S,6S,8R,9S)-2-[(E)-(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-hex-2-enyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane

(4S,5S)-6-Benzyloxy-1-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-4-(2-methoxy-ethoxymethoxy)-5-methyl-hexan-3-one